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Tert-Butyl Acetate

Tert-Butyl acetate, or t-butyl acetate, is a colourless flammable liquid with a camphoror blueberry-like smell. It is used as a solvent in the production of lacquers, enamels, inks, adhesives, thinners, and industrial cleaners. It is also used as an additive to improve the anti-knock properties of motor fuels. tert-Butyl acetate has three isomers: n-butyl acetate, isobutyl acetate, and sec-butyl acetate.

Chemical Properties

Clear, colorless liquid
tert-Butyl acetate or t-butyl acetate is a colorless flammable liquid with a camphoror blueberry-like smell. It is used as a solvent in the production of lacquers, enamels, inks, adhesives, thinners, and industrial cleaners. It is also used as an additive to improve the antiknock properties of motor fuels. tert-Butyl acetate has three isomers: n-butyl acetate, isobutyl acetate, and sec-butyl acetate.

Chemical Properties

Butyl acetates are colorless or yellowish liquids with pleasant, fruity odors. There are 4 isomers.

Physical properties

Colorless liquid with a fruity odor. Odor threshold concentration in water is 4 ppm (CHRIS, 1994). Nagata and Takeuchi (1990) reported an odor threshold concentration of 71 ppbv.
Uses:Gasoline additive; lacquer solvent
Uses Tert-butyl Acetate is a common solvent used in the production of various industrial cleansers, thinners and adhesives and is also known as a VOC.
Uses: As gasoline additive (Wheeler et al.).

Production Methods

Tert-Butyl acetate is prepared from isobutylene reacting with acetic acid in the liquid phase with vanadium pentoxideimpregnated silica as the catalyst and with heat to increase the yield .
Synthesis Reference(s) Organic Syntheses, Coll. Vol. 3, p. 142, 1955
Synthesis, p. 1015, 1987
Tetrahedron Letters, 37, p. 4555, 1996 DOI: 10.1016/0040-4039(96)00902-1

General Description

Colorless liquid with a mild odor. Floats on water. Produces irritating vapor.
 

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Tert-Butyl acetate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. tert-Butyl acetate is incompatible with the following: Nitrates; strong oxidizers, alkalis & acids .

Hazard

Flammable, moderate fire risk. Eye and upper respiratory tract irritant.
Health Hazard INHALATION: Irritation of throat. EYES: Irritation.
Health Hazard Exposure to tert-butyl acetate causes eye, skin, and respiratory irritation in workers. By analogy with the effects of exposure to similar esters, tert-butyl acetate may act as a CNS depressant at high concentrations. The signs and symptoms of acute exposure to tert-butyl acetate include, but are not limited to, itchy or inflamed eyes and irritation of the nose and upper respiratory tract. Exposures to tert-butyl acetate at high concentrations may cause headache, drowsiness, and other narcotic effects.
 

Safety Profile

Poison by inhalation and ingestion. Flammable. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.
Potential Exposure n-Butyl acetate is an important solvent in the production of lacquers, leather and airplane dopes, and perfumes. It is used as a solvent and gasoline additive. sec-Butyl acetate is used as a widely used solvent for nitrocellulose, nail enamels and many different purposes. tert-Butyl acetate is common industrial solvent used in the making of lacquers, artificial leather, airplane dope, perfume; and as a food additive. Isobutyl acetate is used as a solvent and in perfumes and artificial flavoring materials
Environmental fate Chemical/Physical. Hydrolyzes in water to tert-butyl alcohol and acetic acid. The estimated hydrolysis half-life at 25 °C and pH 7 is 140 yr (Mabey and Mill, 1978).

Storage

Tert-Butyl acetate should be stored in a cool, dry, well-ventilated area in tightly sealed containers that are labeled in accordance with regulatory standards. Containers of tert butyl acetate should be protected from physical damage and should be stored separately from nitrates, strong oxidizers, strong acids, strong alkalis, heat, sparks, and open flame. Because containers that formerly contained tert-butyl acetate may still hold product resi dues, they should be handled appropriately.

Shipping

UN1123 Butyl acetates, Hazard Class: 3; Labels: 3—Flammable liquid.
 

Purification Methods

Wash the ester with 5% Na2CO3 solution, then saturated aqueous CaCl2, dry with CaSO4 and distil it. [McClosky et al. Org Synth Coll Vol IV 263 1963, Mangia et al. Org Prep Proc Int 18 13 1986, Beilstein 2 IV 151.]
 

Incompatibilities

All butyl acetates are incompatible with nitrates, strong oxidizers; strong alkalies; strong acids. 

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